diff --git a/src/Umbraco.Core/IO/PhysicalFileSystem.cs b/src/Umbraco.Core/IO/PhysicalFileSystem.cs
index 66ef095b04..e4edb2b86b 100644
--- a/src/Umbraco.Core/IO/PhysicalFileSystem.cs
+++ b/src/Umbraco.Core/IO/PhysicalFileSystem.cs
@@ -304,7 +304,13 @@ namespace Umbraco.Core.IO
             // permissions to reach that path, but it may nevertheless be outside of
             // our root path, due to relative segments, so better check
             if (IOHelper.PathStartsWith(path, _rootPath, Path.DirectorySeparatorChar))
+            {
+                // this says that 4.7.2 supports long paths - but Windows does not
+                // https://docs.microsoft.com/en-us/dotnet/api/system.io.pathtoolongexception?view=netframework-4.7.2
+                if (path.Length > 260)
+                    throw new PathTooLongException($"Path {path} is too long.");
                 return path;
+            }
 
             // nothing prevents us to reach the file, security-wise, yet it is outside
             // this filesystem's root - throw
diff --git a/src/Umbraco.Tests/IO/PhysicalFileSystemTests.cs b/src/Umbraco.Tests/IO/PhysicalFileSystemTests.cs
index 91e764c184..ab9b2cf73d 100644
--- a/src/Umbraco.Tests/IO/PhysicalFileSystemTests.cs
+++ b/src/Umbraco.Tests/IO/PhysicalFileSystemTests.cs
@@ -1,7 +1,5 @@
 using System;
-using System.Collections.Generic;
 using System.IO;
-using System.Linq;
 using System.Text;
 using System.Threading;
 using NUnit.Framework;
@@ -44,6 +42,34 @@ namespace Umbraco.Tests.IO
             return "/Media/" + path;
         }
 
+        private string Repeat(string pattern, int count)
+        {
+            var text = new StringBuilder();
+            for (var i = 0; i < count; i++)
+                text.Append(pattern);
+            return text.ToString();
+        }
+
+        [Test]
+        public void SaveFileTest()
+        {
+            var basePath = Path.Combine(AppDomain.CurrentDomain.BaseDirectory, "FileSysTests");
+
+            using (var ms = new MemoryStream(Encoding.UTF8.GetBytes("foo")))
+                _fileSystem.AddFile("sub/f3.txt", ms);
+
+            Assert.IsTrue(File.Exists(Path.Combine(basePath, "sub/f3.txt")));
+
+            var path = Repeat("bah/bah/", 50);
+            Assert.Less(260, path.Length);
+
+            Assert.Throws<PathTooLongException>(() =>
+            {
+                using (var ms = new MemoryStream(Encoding.UTF8.GetBytes("foo")))
+                    _fileSystem.AddFile(path + "f3.txt", ms);
+            });
+        }
+
         [Test]
         public void GetFullPathTest()
         {
@@ -60,14 +86,31 @@ namespace Umbraco.Tests.IO
             // - does properly normalize separators
             // - does throw on invalid paths
 
+            // works
             var path = _fileSystem.GetFullPath("foo.tmp");
             Assert.AreEqual(Path.Combine(basePath, @"foo.tmp"), path);
 
+            // a very long relative path, which ends up being a short path, works
+            path = Repeat("bah/../", 50);
+            Assert.Less(260, path.Length);
+            path = _fileSystem.GetFullPath(path + "foo.tmp");
+            Assert.AreEqual(Path.Combine(basePath, @"foo.tmp"), path);
+
+            // works too
             path = _fileSystem.GetFullPath("foo/bar.tmp");
             Assert.AreEqual(Path.Combine(basePath, @"foo\bar.tmp"), path);
 
             // that path is invalid as it would be outside the root directory
             Assert.Throws<FileSecurityException>(() => _fileSystem.GetFullPath("../../foo.tmp"));
+
+            // a very long path, which ends up being very long, works
+            path = Repeat("bah/bah/", 50);
+            Assert.Less(260, path.Length);
+            Assert.Throws<PathTooLongException>(() =>
+            {
+                path = _fileSystem.GetFullPath(path + "foo.tmp");
+                Assert.Less(260, path.Length); // gets a >260 path and it's fine (but Windows will not like it)
+            });
         }
     }
 }